Design And Synthesis Of New Functionalized Triptycene-based Molecules

Rigid units are needed to introduce to increase its porosity when designingorganic porous polymer. New aromatic monomers are needed to design andsynthesize to solve the aromatic polyimide excellent performance and poor solubilitycontradictions. It is an effective way to solve the above problems by introducingrigid triptycene structure into these two types of polymers. Triptycene is a uniquerigid three-dimensional aromatic structure, the three benzene rings of triptycenepoint to three directions in the same angle, forming a cavity within the molecule i.e.the free volume between the benzene ring with a benzene ring, each of the benzenering is connected through two single bond to the other benzene ring, the benzenering’s relative movement can not occur. Triptycene special rigid structure is preciselyrequired in the preparation of the organic porous polymer. The solubility oftriptycene-based polyimide is not only increased, will also be formed porouspolyimide as result of hindering the stacking of the polymer chain by triptycene.This article is oriented toward synthesis and applications of porous material andaromatic polyimide. Through an organic molecule design, two anthracenederivatives2,3,6,7-tetramethoxy-9,10-bis (hydrogen/methyl/ethyl) anthraceneand2,3,6,7-tetramethyl anthracene are easily obtained from inexpensive rawmaterials such as1,2-dimethoxybenzene, o-xylene, methylene chloride,acetaldehyde, etc. by Friedel-Crafts reaction. Based on the anthracene derivatives,respectively, by the Diels-Alder reaction with benzyne and1,4-epoxy-1,4-dihydronaphthalene reaction build triptycene derivatives skeleton, and then aftermethoxy demethylation and oxidation of methyl of the triptycene derivativerespectively formed functionalized tetrahydroxy triptycene derivative andtetracarboxylic acid triptycene derivative. Moreover, selective oxidation of methyl intetramethyl triptycene (9,10-o naphthyl anthracene) derivative is explorated.Various intermediates and the target product are characterized by infraredspectroscopy and nuclear magnetic resonance spectroscopy and other necessary means to prove the correctness of the compound structure and reasonable designroute.Functionalized triptycene derivatives we synthesized in simple and efficientsynthetic method have novel structures, can be obtained through cheap raw materialsand be directly used for the synthesis of polymer research. Our research of the thetriptycene functionalized not only contributed to the development of the triptycenechemistry, and paved the way for triptycene applications in high-performancepolymer.